Siesta Key, FL Homes

/16
$1,169,000
- 2 Beds
- 1 Bath
- 1,230 Sq Ft
451 Avenida de Mayo, Sarasota, FL 34242

Welcome to 451 Avenida De Mayo in Siesta Key, FL where unparalleled luxury meets the ultimate island lifestyle. This is the best opportunity right now on the entire island - must move fast - full payout coop buyside. This completely renovated oasis boasts the most coveted location in all of Siesta Key, period. Imagine stepping out your back door to direct boat dock access, while a mere one-minute

Camilo Perez HOME SOLD REALTY LLC

451 Avenida de Mayo, Sarasota, FL 34242
/33
$8,500 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242

Embrace coastal living in this inviting 2-bedroom, 2-bathroom first-level condo nestled within the prestigious Gulf & Bay Club Bayside in Siesta Key, Florida. Step inside to discover a thoughtfully designed space adorned with coastal-inspired décor and an abundance of natural light. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating an ideal space for

Andy Moore GULF COAST REALTY & MANAGEMENT

1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
/2
$1,600,000 Sold Apr 16, 2025
- 2,200 Sq Ft
- $727/SF
- 49 Days On Market
- 3 Beds
- 3 Baths
- Built 1981
6283 Midnight Pass Rd Unit 6283, Sarasota, FL 34242

Discover this RARE and exquisite waterfront condominium home with deeded beach access on Siesta Key! Offering over 36 feet of unparalleled intracoastal water views, this masterpiece is located at Excelsior Beach to Bay. This furnished 3-bedroom, 3-bathroom end-unit residence is situated above your private 2-CAR GARAGE and is located directly on the intracoastal waterway. With hurricane impact

Angela Lista MICHAEL SAUNDERS & COMPANY

6283 Midnight Pass Rd Unit 6283, Sarasota, FL 34242

/27
Est $607,324 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1600 Cove II Place Unit 414, Sarasota, FL 34242

1600 Cove II Place Unit 414, Sarasota, FL 34242

/49
$5,985,000
- 8 Beds
- 6.5 Baths
- 4,094 Sq Ft
538 Canal Rd, Sarasota, FL 34242

Welcome to Sea Spray, a beach and boaters paradise with a private dock across the street and just a block from the famous Siesta Key beach! This eight-bedroom and six-and-a-half-bathroom home boasts a spectacular backyard built like a private waterpark with a Private Resort Style Heated Pool featuring a Rock Water Slide, Waterfall, Grotto, Swim-up bar, Sun Shelf, and Spa. Pack your bags for the

Constantine Stratos COLDWELL BANKER REALTY

538 Canal Rd, Sarasota, FL 34242
/34
$8,000 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242

Experience luxury waterfront living in this stunning 2-bedroom, 2-bathroom condo situated on the second level of Gulf & Bay Club Bayside in Siesta Key, Florida. Boasting breathtaking views of the bay, this meticulously designed residence boasts comfort. Step into a spacious living area adorned with coastal finishes and large windows that invite an abundance of natural light. The open-concept

Andy Moore GULF COAST REALTY & MANAGEMENT

1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242
/2
$615,000 Sold Apr 16, 2025
- 1,352 Sq Ft
- $455/SF
- 222 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
1125 Lake House Cir Unit C112, Sarasota, FL 34242

** THIS HOME WAS NOT AFFECTED BY THE PAST STORMS AND IS MOVE IN READY! ** BREATHTAKING WATERFRONT CONDO WITH PANORAMIC LAKE VIEWS LOCATED ACROSS THE STREET FROM SIESTA KEY BEACH! This stunning condo is everything you have been looking for. The high ceilings, large sliding glass doors and bi-level floor plan gives this home a light, bright and open feeling. When you walk in you will be pleasantly

Kayla Lamb NEXTHOME EXCELLENCE

1125 Lake House Cir Unit C112, Sarasota, FL 34242

/30
Est $568,692 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 872 Sq Ft
5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242

5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242

/49
$997,000
- 2 Beds
- 2 Baths
- 1,094 Sq Ft
385 Avenida Madera, Sarasota, FL 34242

Beaches, Boating & Bistros!!! Excellent Investment, 2nd Home or Build new. Island Style Canal Front Home on Siesta Key, steps to World Famous Siesta Village & the cool quartz sands of Siesta Beach. This Island Style 2 bed, 2 bath home in close proximity to all the food & exciting nightlife that Siesta Key has to offer. 1 car garage. This home on a Cul de sac is light & bright with Terrazzo floors

Dan Miller PREFERRED SHORE LLC

385 Avenida Madera, Sarasota, FL 34242
/38
$5,000 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242

Enjoy your vacation on Siesta Key in this spacious three bedroom/two bathroom vacation rental. This condo is turnkey furnished including washer/ dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.

Andy Moore GULF COAST REALTY & MANAGEMENT

1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242
/2
$470,000 Sold Apr 15, 2025
- 1,101 Sq Ft
- $427/SF
- 40 Days On Market
- 2 Beds
- 2 Baths
- Built 1974
6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242

Condo being sold Turn-Key! Welcome to Paradise on Siesta Key!This charming 2-bedroom, 2-bathroom condo offers 1,101 square feet of coastal living at its finest. Nestled in the heart of Siesta Key, this home is perfect for those seeking a relaxing island retreat or an ideal investment opportunity.Step inside to discover an open kitchen with granite countertops, a convenient

Frank Harris COAST 2 COAST HOME REALTY, PLLC

6157 Midnight Pass Rd Unit E43, Sarasota, FL 34242

/53
Est $681,768 Not Listed For Sale
- 2 Beds
- 2 Baths
- 975 Sq Ft
1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242

1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242

/48
$578,000
- 2 Beds
- 2 Baths
- 920 Sq Ft
1116 S Moonmist Ct Unit M12, Sarasota, FL 34242

Welcome to your tropical retreat on Siesta Key! This beautifully maintained turnkey furnished 2-bedroom, 2-bathroom villa in the desirable Polynesian Gardens community offers the perfect blend of island charm and effortless comfort. Perched on an elevated lot, it features a freshly repainted interior, breezy coastal décor, and all-tile flooring for easy, care-free living. Offering 1,120 total

Christina Gaskill COLDWELL BANKER REALTY

1116 S Moonmist Ct Unit M12, Sarasota, FL 34242
/29
$5,700 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242

Charming 2 bedroom/ 2 bath Condo just a short walk to the beach. Come enjoy our key-west style condo with a very rare 2 car garage. Two swimming pools, tennis court, pickleball, workout room and fishing dock round out the amenities on our lushly landscaped property. Nestled between palm trees, this ground floor condo does not have a unit above it. Impeccably clean and comfortable with a fully

Andy Moore GULF COAST REALTY & MANAGEMENT

1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
/2
$2,100,000 Sold Apr 14, 2025
- 2,758 Sq Ft
- $761/SF
- 64 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1990
3927 Somerset Dr, Sarasota, FL 34242

This gorgoeus home is being sold FULLY furnished, has a dedicated boat dock/lift, pool, private elevator, in a gated community! Somerset Cove is located on the coveted north end of the world-famous Siesta Key, in Sarasota, FL just a short distance to Shell Beach. This premier community, with only eleven (11) homes on property, is island living at its finest! As you pass through the electronic

Patrick Dipinto, III COLDWELL BANKER REALTY

3927 Somerset Dr, Sarasota, FL 34242

/36
Est $741,511 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,270 Sq Ft
5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

/65
$520,000
- 2 Beds
- 2 Baths
- 929 Sq Ft
1300 N Portofino Dr Unit 103, Sarasota, FL 34242

Welcome to your slice of paradise on world-renowned Siesta Key! Located just steps from the powdery white sands of the #1 beach in the U.S., this beautifully updated 2-bedroom, 2-bathroom condo in the highly desirable Siesta Harbor 55+ community is the ultimate coastal retreat. Bright, spacious, and thoughtfully designed, this residence features stylish luxury vinyl flooring, a beautifully

Rachelle Golden MICHAEL SAUNDERS & COMPANY

1300 N Portofino Dr Unit 103, Sarasota, FL 34242
/34
$8,100 per month
- 2 Beds
- 2 Baths
- 1,420 Sq Ft
- Condo for Rent
1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242

Welcome to your Gulf & Bay Club Bayside sanctuary in the heart of Siesta Key, FL! This second-story bay front condo offers a blissful retreat with breathtaking views of the azure waters. With two bedrooms and two bathrooms, this meticulously designed residence seamlessly blends coastal elegance with modern comfort.Step into a sunlit living space adorned with coastal-inspired décor,

Andy Moore GULF COAST REALTY & MANAGEMENT

1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242
/2
$870,000 Sold Apr 14, 2025
- 1,361 Sq Ft
- $639/SF
- 79 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
5780 Midnight Pass Rd Unit 408, Sarasota, FL 34242

RESORT STYLE LIVING IN THIS EXQUISITELY RENOVATED 2-BEDROOM/2-BATH CONDO. THE LANAI FRAMES THE VIEW OF THE SPARKLING WATERS OF GULF OF MEXICO & AMAZING SUNSETS. OPEN FLOOR PLAN WITH SPACIOUS LIVING ROOM/DINING ROOM WITH SLIDERS TO THE LANAI. KITCHEN FEATURES QUARTZ COUNTERS, ALL STAINLESS STEEL APPLIANCES, DECORATIVE TILE BACKSPLASH & WOOD PAINTED CABINETRY WITH ADJACENT BREAKFAST ROOM. LARGE

Betsy Campbell MICHAEL SAUNDERS & COMPANY

5780 Midnight Pass Rd Unit 408, Sarasota, FL 34242

/33
Est $663,474 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
5963 Midnight Pass Rd Unit 339, Sarasota, FL 34242

5963 Midnight Pass Rd Unit 339, Sarasota, FL 34242

/100
$6,499,500
- 10 Beds
- 10 Baths
- 7,052 Sq Ft
1204 Derby Ln, Sarasota, FL 34242

Experience luxury coastal living at its finest with this exceptional three-story estate located in the coveted community of SIESTA KEY! Built in 2017 to the highest building standards, this exclusive property boasts TEN (10) bedrooms, EIGHT (8) full bathrooms, (2) half baths and TWO (2) private heated pools, TWO (2) outdoor kitchens and FOUR (4) car garage. Situated just a short walk through a

Jeffrey Stuben CHARLES RUTENBERG REALTY INC

1204 Derby Ln, Sarasota, FL 34242
/24
$7,600 per month
- 2 Beds
- 1 Bath
- 959 Sq Ft
- Condo for Rent
1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242

Gulf and Bay Club Bayside is one of the most attractive condominium units on Siesta Key. This beautifully remodeled unit offers luxury accommodations at a reasonable cost. Offering a beautiful lake view and steps to the resort-style pool. You will enjoy your stay every minute.Enjoy all of the luxurious amenities this unit has to offer, from comfortable King size bed to the comfy

Andy Moore GULF COAST REALTY & MANAGEMENT

1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
/2
$3,300,000 Sold Apr 10, 2025
- 3,362 Sq Ft
- $982/SF
- 14 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2009
317 Beach Rd, Sarasota, FL 34242

ONE-OF-A-KIND IN THE HEART OF SIESTA KEY! With more than 3,300 square feet of beautifully designed living space, this meticulously maintained 4-bed, 3.5-bath single-family home is move-in ready and available for a quick close, as it sustained NO storm damage. From the moment you arrive, the classic architecture, tile roof and detailed craftsmanship are bound to leave a lasting impression. The

Christa Spalding COLDWELL BANKER REALTY

317 Beach Rd, Sarasota, FL 34242

/49
Est $688,472 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 975 Sq Ft
1140 W Peppertree Ln Unit 114, Sarasota, FL 34242

1140 W Peppertree Ln Unit 114, Sarasota, FL 34242

/38
$1,125,000
- 3 Beds
- 3.5 Baths
- 1,767 Sq Ft
5108 Saint Albans Ave, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer | BEACH VIBES? Check, PRIME LOCATION? Check, HIGH END RENOVATIONS all completed in 2025? Check, check & check! Welcome to the ultimate in Florida living – whether you are looking to settle in full time or score an amazing SHORT TERM RENTAL/VACATION HOME, this one is a MUST SEE! Located in the

Jennifer Wemert WEMERT GROUP REALTY LLC

5108 Saint Albans Ave, Sarasota, FL 34242
/18
$7,700 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242

Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops

Andy Moore GULF COAST REALTY & MANAGEMENT

1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
/2
$2,300,000 Sold Apr 10, 2025
- 4,071 Sq Ft
- $565/SF
- 299 Days On Market
- 4 Beds
- 4 Baths
- Built 1979
5422 Siesta Cove Dr, Sarasota, FL 34242

One or more photo(s) has been virtually staged. Home has sustained significant water damage on the first floor. Rehab or build your dream home on 90 feet of water frontage in Siesta Cove, a highly sought after neighborhood on the North end of Siesta Key. Unobstructed views of the Intracoastal, Phillippi creek and downtown. 10 minute walk to the public beach, biking distance to the village.

Tori Harless COLDWELL BANKER REALTY

5422 Siesta Cove Dr, Sarasota, FL 34242

/41
Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,463 Sq Ft
5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242

5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242

/37
$685,000
- 2 Beds
- 2 Baths
- 929 Sq Ft
1350 N Portofino Dr Unit 402, Sarasota, FL 34242

UNUSALLLY AVAILABLE! DIRECT INTRACOASTAL VIEW! Stunning ICW Water View on Siesta Key with direct, full view of the Intracoastal Waterway and private beach access across the street. Sought-after Tarpon Building in Siesta Harbor 55+ Community with only 8 units facing directly to the main Intracoastal waterway-- Views are Outstanding! Open Floor Plan, large open dining and living room leading to

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1350 N Portofino Dr Unit 402, Sarasota, FL 34242
/89
$4,700 per month
- 3 Beds
- 3 Baths
- 1,867 Sq Ft
- Condo for Rent
4900 Ocean Blvd Unit 501, Sarasota, FL 34242

Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the

Beth Dilley ASCENDIA REAL ESTATE

4900 Ocean Blvd Unit 501, Sarasota, FL 34242
/2
$807,500 Sold Apr 09, 2025
- 1,173 Sq Ft
- $688/SF
- 12 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
6202 Midnight Pass Rd Unit 201, Sarasota, FL 34242

Nestled in the heart of Siesta Key, this beautifully updated and turnkey furnished corner garden unit at the iconic Siesta Dunes Resort offers the perfect blend of comfort, style, and location. Situated on the second floor, this 2-bedroom, 2-bathroom unit has been meticulously updated to provide a luxurious coastal retreat.Interior Features / updates include:*Luxury Vinyl Flooring

Ryan Carson RE/MAX ALLIANCE GROUP

6202 Midnight Pass Rd Unit 201, Sarasota, FL 34242

/38
Est $644,027 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

/41
$1,500,000
- 3 Beds
- 3 Baths
- 1,658 Sq Ft
5169 Oxford Dr, Sarasota, FL 34242

Welcome to 5169 Oxford Drive, a beautifully renovated waterfront home located in the heart of Siesta Key, Sarasota. This 3-bedroom, 3-bathroom residence offers the perfect blend of coastal charm and modern luxury, thoughtfully updated in 2021 with high-end finishes throughout. Inside, you'll find over 2,000 square feet of open living space featuring soaring ceilings, crown molding, and luxury

John Chalkias CHARLES RUTENBERG REALTY ORLANDO

5169 Oxford Dr, Sarasota, FL 34242
/35
$8,200 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242

Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are

Andy Moore GULF COAST REALTY & MANAGEMENT

1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
/2
$1,125,000 Sold Apr 07, 2025
- 1,645 Sq Ft
- $684/SF
- 16 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
1341 Siesta Bayside Dr Unit 1341B, Sarasota, FL 34242

Nestled in the highly coveted Gulf & Bay Club Bayside, this 3-bedroom, 2-bathroom townhouse-style condominium offers breathtaking water views, resort-style living, and the flexibility of weekly rentals – perfect for personal enjoyment or as a lucrative income-producing property. Situated along the peaceful Intracoastal Waterway, this 1,645 sf. property blends comfort, luxury, and income potential

Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

1341 Siesta Bayside Dr Unit 1341B, Sarasota, FL 34242

/31
Est $536,827 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 900 Sq Ft
1110 S Moonmist Ct Unit M-11, Sarasota, FL 34242

1110 S Moonmist Ct Unit M-11, Sarasota, FL 34242

/17
$699,000
- 2 Beds
- 2 Baths
- 1,577 Sq Ft
782 Birdsong Ln, Sarasota, FL 34242

Opportunity knocks in one of the most sought-after locations on Siesta Key! Roof in good shape and impact windows throughout the home. This prime property offers the perfect chance to create your ideal coastal retreat. Situated just moments from world-famous Siesta Key Beach, this lot presents a blank canvas for a stunning new build or a visionary renovation. Currently, the property features a

Joey Lamielle RE/MAX ALLIANCE GROUP

782 Birdsong Ln, Sarasota, FL 34242
/27
$6,300 per month
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Condo for Rent
1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242

Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area,

Andy Moore GULF COAST REALTY & MANAGEMENT

1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
/2
$965,000 Sold Apr 04, 2025
- 1,737 Sq Ft
- $556/SF
- 165 Days On Market
- 3 Beds
- 2 Baths
- Built 1982
1271 Dockside Place Unit 215, Sarasota, FL 34242

Experience coastal living in this HIGH and DRY waterfront 3-bedroom, 2-bathroom condo on the sought-after Siesta Key. Perfectly positioned just steps from the renowned Siesta Key Beach, this second-floor gem offers unparalleled access to sun and sand, while a private boat slip and lift awaits your boating adventures.This turnkey-furnished condo is meticulously designed for both relaxation

Debra Forkan COLDWELL BANKER REALTY

1271 Dockside Place Unit 215, Sarasota, FL 34242

/69
Est $686,069 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
5855 Midnight Pass Rd Unit 704, Sarasota, FL 34242

5855 Midnight Pass Rd Unit 704, Sarasota, FL 34242

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